Methanol → 2-Thioadenosine

Participants

Reaction Steps

To 10.0 g of 5-amino-1-β-D-ribofuranosylimidazole-4-carboxamide oxime hydrochloride were added 120 ml of methanol and 120 ml of pyridine to form a solution. 60 ml of carbon disulfide was added to the solution, and the resulting mixture was allowed to react in an autoclave at 120° C for 3 hours under autogenous pressure (about 10 kg/cm2). The reaction mixture was concentrated to dryness, and the residue was dissolved in 1N aqueous ammonia. 100 ml of n-butanol and 50 ml of glacial acetic acid were then added to the solution followed by cooling to crystallize the product to obtain 9.01 g of 2-thioadenosine having a melting point of 199° C (with decomposition) in an 88% yield.

Provenance & Evidence